1,4-Dibromobutane → HCID 59395622, compound

HRID 1097726Notes

Reaction equation

HRID 1097726 reaction equation
[C:1]1([CH2:7][CH:8]2[CH2:12][CH2:11][NH:10][C:9]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.CC(C)([O-])C.[Na+]>CN(C=O)C>[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][N:10]1[CH2:11][CH2:12][CH:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:9]1=[O:13]

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 102412993-benzylpyrrolidin-2-oneHCID 23676156Sodium t-butoxide

Product 1

HCID 59395622HCID 59395622, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(phenylmethyl)-2-pyrrolidinone (0.23 g, 1.3 mmol) and 1,4-dibromobutane (0.57 g, 4.2 mmol) in DMF (5 ml) was added sodium t-butoxide (0.151 g, 1.6 mmol) and the solution stirred for 18 h. The solution was concentrated and the residues chromatographed over silica (20 g SPE, eluting first with cyclohexane then with DCM) to provide the title compound as a colourless oil containing a trace of DMF (0.25 g, 61%).

Workup

  1. concentrationThe solution was concentrated
  2. customthe residues chromatographed over silica (20 g SPE
  3. washeluting first with cyclohexane

Sources & evidence

ORD record
ord-9a796ec6e3354d3d8f11d4c5af5494ac
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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